Jay Whiss is Bringing Toronto to the World

On the heels of his debut solo album Peace of Mind, Jay Whiss reflects on Toronto and the stories that have shaped him.

It’s been a long and winding road for Jay Whiss. For years, the “Dark Cloud” rapper has been a staple in the Toronto rap scene as part of the Prime Boys, while also carefully putting out a steady stream of his own projects. Jay and his fellow Prime Boys members, Jimmy Prime and Donnie, have always embodied Toronto to the core (Jimmy is even credited with coining the ‘6ix’) and you can’t really talk about the city’s hip-hop scene without mentioning them. But if you asked Jay at any point along the way, his goal always stretched far beyond the city’s limits. 

While Jay has always had his sights fixed on bigger things down the line, he prefers to live in the moment and appreciate what’s in front of him right now. “I don’t catch my chickens before they hatch,” he says firmly. “I’m kind of just along for the ride.” For Jay, that means not skipping any steps and enjoying the process on the way to realizing his dreams – and his debut solo album, Peace of Mind, does just that. 

Working his way up from the bottom, Jay, who didn’t even write his first track until he was 16, is finally ready to introduce himself and the Esplanade rap scene to the world. “I’m painting a picture of who I am and what I stand for,” he says. “I owe it to any listener to offer a perspective of me. It gives them a rundown of who I am as a whole.” 

Jay hails from the Esplanade neighbourhood in Toronto’s downtown core. The bustling area runs parallel to the city’s central waterfront and consists mostly of low-rise residential buildings. It was the Prime Boys that made ‘176’ well-known in Toronto, a moniker that refers to a subsidized housing unit in the area, putting the Esplanade firmly on the map. 

Growing up in Toronto has given Jay a unique perspective on things. The diverse makeup of the city and the unique perspective of a Canadian in the hip-hop world have given him a different way of looking at things. He’s always had a unique approach that has separated him from the pack and given him an outsider’s perspective, but Jay isn’t the type to make any excuses. “In Toronto, we have all the avenues we need,” he adds.

Jay Whiss - LYFSTYL

However, it’s the sense of family that makes him proud to represent his roots. There are a few other big-time acts that call the Esplanade home, including SAFE and fellow Prime Boy member Donnie. Along with Jimmy Prime and a long list of collaborators, they are the faces defining the local scene, but they’ve always been a close-knit group even before they started making music together.

One of his first bonds was with Donnie, who was friends with Jay dating back many years now. “We were just chilling one day at 176 and he asked me to go to the studio,” he recalls. “I booked us a session at Wellesley Sounds and there were probably 20 of us who walked over there. We had the session and everything with Donnie just started from there.” 

Jay exclusively creates music with people that he considers his family to this day. It’s important for him to surround himself with not only like-minded individuals but also people he really connects with the outside of music. It’s become a mantra for Jay when carefully selecting who to work with. 

Among the other frequent collaborators including multi-platinum producer Murda Beatz. The two met through music years back and hooked up on their single ‘Brown Money’ and became really close. “We connected because we both have lots of aspirations,” he says. “The level of understanding is on a different level.” He’s a firm believer that it’s the relationship they share on a personal level that allows their music to flourish the way it does. “Sometimes you can be friends but walk on different paths,” he reflects. “It’s just natural with Murda though because we’re both making music and on the same path.” 

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Music has always been a vehicle that’s helped Jay to get through a lot in his life. His projects are a collection of feelings, lessons and stories, so it’s no surprise that his cerebral songwriting and lyrical prowess have become hallmarks of his sound. “It was always a way to express myself,” says Jay. “I don’t even know what drew me to it, to be honest. It was a way to get things off my chest.” It’s always been about giving listeners that same feeling that he had in creating the music. “Like capturing a feeling,” he says calmly. 

What Jay does especially well is taking his experiences – good and bad – and channelling those raw emotions into thoughtful lyrics and well-executed sounds. “That was always my intention,” he says. “Making music from somewhere rather than just making something that sounds cool, you know?” 

This was on full display a couple of years ago when Jay lost two of his closest friends to gun violence. Leading up to the release of a Prime Boys project, tragedy struck and Jay’s life changed forever with the daylight murders of 21-year-old Regent Park rapper Smoke Dawg and 28-year-old Koba Prime. Smoke Dawg was a longtime collaborator and friend, and Koba was the Prime Boys’ assistant manager. In the weeks that followed, Jay would bury two of his closest friends in back-to-back ceremonies alongside a mourning Toronto hip-hop community. 

The Dark Cloud EP served as a reflection of Jay’s state of mind during this time. Through this introspective and melancholic project, Jay displayed both his pain and self-growth with heavy imagery that features grey clouds and intense shadows. On his newest album, the track “Mind in a Maze” also garnered some attention to turn his emotions into well-crafted sounds after some time has passed. 

“I got roses in my hand and a heart full of pain / I can’t believe I’m losing friends / I’m still crying to this day.” – Mind in a Maze

Not only does Jay’s music show that he can overcome difficult times, but it also shows his progression as an artist and as a person. It was his resilience in his darkest hours that ignited their strength to keep going and craft something all his own. “When you write it down and record it, it helps put things in perspective and to dig deep into your own thoughts,” he says. “I’m trying to get my deepest thoughts out onto the song. It’s way more therapeutic when you can do it verbally.” 

Jay is leading the Esplanade rap scene and spreading messages of positivity rather than hostility across the city. His music is for “anybody who’s going through anything” and sparks hope in a rapidly changing city. At the end of the day, Jay hopes that people can take something from his thoughts, emotions and stories – and hopefully learn from it. “It’s about bettering yourself and making the most out of your situation and the cards you’ve been dealt,” he says. “I wasn’t given the best hand or deck of cards, but I’m making the most out of what I have. Someone’s always going to have it harder than me, so I don’t really throw myself pity parties or anything like that.”

Jay has learned a lot along his journey and among those lessons is to take nothing for granted. While he speaks about the world with a tone of hope and optimism, he’s blunt at the same time. It’s something that’s allowed him to be honest with himself and reach this point. “Don’t ever feel sorry for yourself,” he adds. “There’s always going to be someone who’s going through more than you. So take it on the chin and try to most the most of your life.” 

No matter where his music takes him, Jay is learning to keep everything in perspective. “This is where I’m at my best,” he says. “I just love what I do so much. I’m fortunate in the sense that I can flourish doing something I love.” 

Peace of Mind gives us a timeless glimpse into exactly who Jay Whiss is. The 10-track album is a culmination of all his experiences and growth in Toronto – the stories that have shaped the person you see today. He’s eager to bring the Esplanade rap scene to the world and you get the feeling that Jay is just beginning to hit his stride.

Words by Braeden Alexander – Stream Jay Whiss’ debut LP now

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